Paths the mind follows: Doubt and discovery pedaling 100 miles
Halfway along the Glacial Drumlin State Trail, headed east.
Quests are overrated. Adventures are fine, if you take them at face value, but there is great risk in overestimating their importance. And although they say so much in life is about the journey, not the destination, some journeys are miserable and the destination can’t come fast enough.
This may seem like a self-defeating introduction to the story of my own recent quest that I hope you’d actually read through to the end — a dubious mission, should you choose to accept it. It reflects my trail vision, some of the thoughts floating across my mindscape as I struggled to pedal my bike forward with feet sore, legs sore, butt sore, arms sore, neck sore and eyes looking for a place to fill up on water.
I succeed, technically. I reached my destination. But after most of a day and 100 miles spent on a bike from Madison to Milwaukee, rather than a sense of achievement, I felt the unexpected weight of doubt. I sincerely wondered to myself, why did I just do that?
To be clear, when I use the word “quest,” I’m applying it specifically and narrowly to endurance feats, which have no practical value in daily life. By another name, you can refer to them as goals of varying severity, the kind that often inspire amateur athletes like me to try harder, do more. Runners and cyclists have a grab bag of familiar quests to choose from. Marathon training can be its own journey, even before a runner makes it to race day. And one key benchmark for cyclists is the century ride, 100 miles, a distance that can be done in a day but requires a build-up of at least a few preparatory long rides.
The century ride provided the foundation for this particular two-wheeled quest of mine.
But why? What motivates any runner or cyclist to embark on activities beyond what one normally would expect of the self? The more I thought about that question, I realized there are far too many potential answers. One obvious one is health and fitness. We train to get in shape. Some people are specifically focused on weight loss, or slowing down weight gain. A related motivation is physical attractiveness. Working out is supposed to make you look good, and working out hard is supposed to make you look better. Build the body, feed the ego. Certainly, a lot about of endurance sports is driven by outsized egos. Narcissism? You will get no judgment from me. At least at this time.
There’s a different strain of endurance quest that seeks opportunities to test the limits of human ability. Humans were never meant to live on the top of Mount Everest, and it’s arguably not a good idea to even climb there, but a quest like that has a certain allure. There can be a spiritual dimension to such adventures, as if putting the body through excessive, unnecessary toil can bring someone closer to the divine. Even so, a belief in God is not necessary to find motivation in the more secular language of transcendence. Some of us hike that mountain or pedal many miles or run the distance because we need to transcend our ordinary selves and want to end up a different person at the end. This is the quest of individual enlightenment through calculated suffering.
Transcendence has a personal appeal to me, and looking back on my own past endurance quests, typically completed alone, this comes closest to how I would usually explain my own motivation. After my recent century ride, however, I’m not sure it’s accurate anymore.
If I’m being honest with myself? I think the real reason I would do something like ride 100 miles across the state of Wisconsin is that middle-aged life has grown rather pedestrian, and I need crazy quests to shake up the status quo of the mundane.
Short translation: I biked because I was bored.
● ● ●
When did I begin to doubt the necessity of this particular 100-mile quest? I think it was around mile 70. I had rolled into Dousman after about 40 miles on the Glacial Drumlin State Trail. I stopped there with little more than a Cliff Bar filling my stomach, my water bottles empty and my bladder full. It was break time, whether I wanted one or not. There was a makeshift aid station set up outside the Bike Doctor, a trail-side business. On that Saturday, the Bike Doctor was leaning in to that weekend’s Ride Across Wisconsin.
Yes! I was biking halfway across Wisconsin on the same weekend that a huge group of OTHER cyclists were biking across the whole state, from La Crosse to Milwaukee. Most took two days. A brave few attempted it in a single day, and they were the ones the Bike Doctor was setting up for. But those riders wouldn’t be coming through looking for break until later in the day. I was riding solo and not registered for the RAW but still figured I could justify taking advantage of this stop, which basically meant using the porto-potty and then sitting on a bench for 15 minutes.
I took off my shoes and stretched my toes. Shoes by Shimano, my first pair of cycling cleats, purchased for $75 before this ride. With matching pedals, also $75. Was I really a serious cyclist now? The legs didn’t feel that way. Feet in pain, I swapped out a new pair of socks. I also put on a new shirt and stuck my sweat-drenched old shirt into my pack along with the old socks. Only a little more than 30 miles to go, I thought, as I sat there at the side of the trail. I didn’t fear those last 30 miles, but I didn’t crave them either. On any other day, I might have ended my ride there, thrown the bike into the van, driven home, and it would have felt like a fine excursion. Except, today I couldn’t. I was on a quest that had to be completed! Impossible to give up now.
The time to give up would have been at 5 p.m. — yesterday.
I had finished up work Friday afternoon and was quickly throwing my things together to head out the door. Everything I needed I crammed into a Camelbak bag: ID, credit card, keys, sunglasses, change of clothes, bandanna, sneakers. After a final inspection of the bike, a Jamis Aurora, I said goodbye and at 5:15 pointed the front tire toward the train station. A central component of my vision, my quest, was to go intermodal. I had a ticket ($23.70) on the Badger Bus and pedaled to the Milwaukee Intermodal Station in time for a 6 p.m. departure. The driver informed me that he normally would have collected an additional $10 for stowing the bike under the bus, but he let me on for free. Feeling lucky!
The idea for a cross-Wisconsin bike trip had been percolating for several years. My only other century ride, in October 2020, was a kind of test run. That ride, accompanied for part of the way by cycling friends Keith and Bob, took me from home in Wauwatosa to Lake Mills, mostly on the Glacial Drumlin, and then back to Greenfield Park, where my wife and sons picked me up in the minivan.
This time, the Badger Bus ride down I-94 got me to UW-Madison around 7:30 p.m. I walked down Lake Street to a grocery store to pick up a banana, a granola bar and a Clif Bar. Then I biked around Madison a bit, looking for a Thai restaurant. I finally found some Pad Thai at a place called Asian Noodle ($13.66). Carrying the food in a bag by hand, I plotted my route around the south shore of Lake Monona. Wisconsin’s Capitol shone bright across the water as I pedaled through the peaceful twilight. It was a terrific evening, but I wasn’t looking to stay out late. Tonight’s destination was the Avid Hotel on Broadway ($41.30 after a nice Hotels.com credit). I ate my Pad Thai in the room, my bike propped against the wall, and turned out the light at 9:30. I fell asleep wondering what kind of adventure the next day would hold.
● ● ●
Alarm at 5:30, I was up and moving. Time to try on the padded-butt shorts and anti-chafing lotion I had picked up for this ride ($41.20). Seemed like a good fit. Everything else into the pack, and I was out the door by 6 a.m., right on schedule.
Here’s my assurance that I won’t bore you with the play-by-play of every mile of this journey. Seriously, I don’t understand how anyone could find endurance sports interesting to read about, and yet whenever I meet up with friends or fellow amateur athletes for a ride or run, it’s amazing we can find so much to talk about. The gear. The training. The strategies. The injuries. The recovery. Any number of details that probably would only be of interest to fellow travelers in the moment of sharing. After the fact, to think back and try to put into words the experience of something like riding from my hotel in Madison to the lakefront in Milwaukee would seem on the surface to be a dull endeavor.
And yet. … That Capitol! What a thrill to pedal at daybreak around Lake Monona and then up the hill to Madison’s famous square. I circled it while vendors were setting up at 6:30 for the morning’s farmer’s market. Then the ride really got underway, as I found my way to the Capital City State Trail and south to the Lower Yahara Trail. Few things on this ride were as beautiful as the sun bursting through the clouds over the Lower Yahara’s long boardwalk bridge, a picturesque combination of human engineering and natural landscape. The Yahara River is a real treasure, and I have it in my mind to attempt another quest someday in which I paddle the river from Lake Mendota to the Rock River. Someday.
On this day, however, after leaving the trail, my initial reverie was waylaid by some challenging country roads. I was following the map in my mind to get to Cottage Grove. A slight wrong turn added a few miles onto my trip. I made a quick stop by some farmland to check Google Maps and get myself back on track. I had been keeping up a strong pace of nearly 16 mph — there’s the ego working — but not sure I’d be able to maintain it. When I finally reached the start of the Glacial Drumlin, it became apparent that my previous speed goal was far too ambitious. Dirt and gravel is a reality check for any cyclist’s inflated ego, and at mile 30 I left the hard asphalt behind.
What was my strategy for this ride? Well, I didn’t really have one. Just pedal, dammit. My only plan was to break it roughly into thirds, and the first third ended with a cup of coffee and a blueberry muffin at the Deerfield Coffeehouse ($6.25). The body felt good, other than my cramped toes, and for a moment I confused this long quest for a brief, leisurely jaunt. Cheers to you, fellow weekend cyclists! Let’s all enjoy the ride!
Good luck keeping spirits up that high. Because the second leg of the journey was another 30+ miles on the same dirt-and-gravel trail, almost all of it straight and with minimal variation in the scenery. Rail trails are not my favorite, but for a ride like this, the tedium can be an asset, if you can rack up the miles while zoning out. There were some nice lake-side vistas through Lake Mills. Otherwise, it was pedal, pedal, pedal at what felt like a slower and slower pace. I passed walkers, runners and other cyclists here and there, but for the most part it was a solitary ride. The one exception was around Helenville, when I passed an older man who was standing next to his bike at a crossroads. A bit later he caught up to me and started to chat. Said he lived on a farm down the trail and regularly biked on the Glacial Drumlin, since it was just a short distance out his door. He asked if I was connected to the RAW event, and I explained no, just some crazy solo cyclist trying to complete a silly quest. At another crossroads, he turned back toward home and I never saw him again.
I regret not asking his name. These are the kinds of details that fuel that nagging doubt: Maybe this quest wasn’t a good idea, or maybe I’m not doing it for the right reason. Why wouldn’t I ask him for his name?
● ● ●
Though nameless, he had provided me with a break from the mental monotony of the trail ride. Now that I was back on my own, I was desperate to be more miles along. How much farther until Dousman? It felt like an eternity, but I made it. There was just the final third to go, but nothing about that last stretch expected to be easy. The final 30 miles felt as hard as the first 70, and not even the downhill from Wales to Waukesha seemed to make much difference. I was just going through the motions at this point, doing just what it took to check this quest off the list and go home.
That meant reaching the end of the Glacial Drumlin in Waukesha, navigating city streets to the New Berlin Trail, which connects to Greenfield Park, which links to the Oak Leaf Trail and then the Hank Aaron State Trail. That’s what brought me into downtown Milwaukee and finally to the red lighthouse just beyond Milwaukee’s iconic Hoan Bridge. As I propped my bike against the lighthouse for a photo and took a separate selfie of myself, I felt relief and briefly a sense of accomplishment, but why? What had I really accomplished? My wife was nearby with the van to pick me up, and that drive home felt more consequential than all 100 miles on the bike had. Did I just waste 24 hours of my life on a physically demanding and time-consuming task with nothing to show for it other than the obligatory Strava evidence and some activity kudos?
My defiantly simple answer: No, it wasn’t a waste. Despite my self doubt, I was and remain convinced that this quest was worth it. When I was a younger man, I would have seen this solitary slog as a goal in itself, and at the end, I would have felt spiritually rejuvenated by the experience, as if a hundred new perspectives on life had been revealed to me. But look, I’m 46. At some point, I think a person needs to accept that there might not be a hundred new perspectives left to be revealed. At this age, I’d be happy just for one or two now and then.
At least one or two new perspectives were possible on this ride, and I feel fortunate for them. It occurred to me that the most obvious lesson from this ride was that going solo is less appealing than finding friends and family to ride with — or to do anything with. I don’t crave absolute solitude the way I once did.
And if there was a reason for completing this ride, it wasn’t to achieve transcendence. I wasn’t going to come out the other end of those 100 miles as a different person or even a slightly changed person. What I got instead was an opportunity to learn something about myself, even if it was just the knowledge of how this 46-year-old body and mind would react to such a quest. And some thoughts can only form when fired in the crucible of a dubious feat of endurance. They certainly won’t form during the normal 9-to-5 slog of workaday life.
There’s another reason to go on a quest like this, or any quest. It gives a writer something to write about. Maybe that’s the accomplishment I was secretly looking for. I might have to try it again and see.